Remington, Wood Berry, and Medfield border Hampden and are also great places to look.

Delaware, Maryland, and Virginia share way to many borders between at least 2 of the states for an area of that size to make sense being considered a single market

But its not unlike gambling in a casino.  

So many others "settle" and take the deal in hopes for higher sales prices in time, they are literally gambling on continued appreciation to take the deal down.

I'm a bit weary of choosing a property that already has a tenant in place (section 8 tenant or not), because it always feels like a bit of a gamble.

Are you willing to gamble the $2,500 that your going to find a buyer?

You really need to find yourselves an accountant and attorney with cross-border real-estate experience and find the organisational structure which best meets your needs.Where you will be five individuals, entering this venture, @Matthew Lee is correct about doing a level set with everyone, before monies are committed.  

Saw these while exploring around Newark yesterday in the bordering neighborhood in Harrison NJ (East Newark).

Better yet look closer to MA border.

This sounds a lot like gambling?